N-Boc-D-proline

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Cat Number

INT37784171

CAS Number

37784-17-1

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CAS Number

37784-17-1

EINECS

1533716-785-6

Storage

2-8℃

Synonyms

(R)-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER;T-BUTYLOXYCARBONYL-D-PROLINE

Molecular Formula

C10H17NO4

Molecular Weight

215.25

Smiles

N1(C(OC(C)(C)C)=O)CCC[C@@H]1C(O)=O

Appearance

White to off-white solid

Melting Point

134-137℃

Boiling Point

355.52℃

Relative Density

1.18

General Description

N-Boc-D-proline is the N-tert-butoxycarbonyl protected derivative of D-proline, a cyclic amino acid. This protected form of the unnatural D-enantiomer is essential for the construction of peptides with specific chirality.

Mechanism of Action

It functions as a rigid cyclic building block in peptide synthesis. The secondary amine in the pyrrolidine ring is protected by the Boc group, allowing for regioselective peptide bond formation while maintaining the D-configuration of the proline residue.

Application

It is widely used in the synthesis of peptidomimetics, chiral catalysts, and as a component in peptide-based drugs where D-proline is required to alter metabolic stability or biological activity.

The development of an achiral Eu(III)-containing polymer complex (P-2) as a circular dichroism (CD) probe for the enantioselective recognition of N-Boc-proline enantiomers was reported. The polymer was synthesized via Sonogashira coupling, incorporating a β-diketonate unit in the main chain, which coordinates with Eu(TTA)ₓ to form the luminescent complex. Upon the addition of chiral N-Boc-proline, the polymer complex exhibited a strong Cotton effect in the CD spectra, with a negative response for N-Boc-L-proline and a positive response for N-Boc-D-proline. These mirror-image CD signals arise from coordination induction between the chiral proline enantiomers and the Eu(III) complex moiety. The study further demonstrated a linear relationship between the molar ellipticity and the concentration of both N-Boc-L-proline and N-Boc-D-proline, confirming the quantitative sensing capability. Importantly, the probe showed superior CD response toward N-Boc-proline compared to other N-Boc-protected amino acids.

Fig. 1 (a) Structure of the achiral polymer complex P-2; (b)N-Boc-L- or D-Proline. (Dai C.; et al. 2014)

References

Dai C, et al. Chiral sensing of Eu (III)‐containing achiral polymer complex from chiral amino acids coordination induction. Journal of Polymer Science Part A: Polymer Chemistry, 2014, 52(21): 3080-3086.